N-(3-{5-[3-(acetamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)acetamide → N-(3-{5-[3-(Acetylamino)propyl]pyridin-2-yl}propyl)acetamide

HRID 49573Notes

Reaction equation

HRID 49573 reaction equation
[C:1]([NH:4][CH2:5][C:6]#[C:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[N:12][CH:13]=1)(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])=[N:12][CH:13]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 11369220N-(3-{5-[3-(acetamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)acetamideHCID 178418361HCID 178418361, compound

Product 1

HCID 11173477N-(3-{5-[3-(Acetylamino)propyl]pyridin-2-yl}propyl)acetamideYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of N-(3-{5-[3-(acetamido)prop-1-ynyl]pyridin-2-yl}prop-2-ynyl)acetamide (2-1) (10 g), 10% Pd/C (1.5 g) in methanol (200 mL) was hydrogenated under 20 psi hydrogen at room temperature for 16 hours. The catalyst was removed by filtration using Solka-floc and washed with methanol. The filtrate and washings were combined and concentrated under reduced pressure to provide 10-1 as a crystalline compound (10.1 g); m.p. 95.2-97.8° C.

Workup

  1. customThe catalyst was removed by filtration
  2. washwashed with methanol
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-712f4fc7a63040e09e80b5224a654808
Source dataset
uspto-grants-2004_03
Patent number
US06706885B2

Reaction notes

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